diff --git a/ElementX/Sources/Screens/MediaPickerScreen/PhotoLibraryPicker.swift b/ElementX/Sources/Screens/MediaPickerScreen/PhotoLibraryPicker.swift
index 5bbb5eeb7..2812bb810 100644
--- a/ElementX/Sources/Screens/MediaPickerScreen/PhotoLibraryPicker.swift
+++ b/ElementX/Sources/Screens/MediaPickerScreen/PhotoLibraryPicker.swift
@@ -34,7 +34,7 @@ struct PhotoLibraryPicker: UIViewControllerRepresentable {
 
     func makeUIViewController(context: Context) -> PHPickerViewController {
         var configuration = PHPickerConfiguration(photoLibrary: .shared())
-        
+        configuration.selection = .ordered
         configuration.selectionLimit = switch selectionType {
         case .single:
             1
@@ -86,18 +86,21 @@ struct PhotoLibraryPicker: UIViewControllerRepresentable {
             
             Task {
                 let selectedURLs = await withTaskGroup { taskGroup in
-                    for result in results {
-                        taskGroup.addTask { await self.processResult(result) }
-                    }
-                    
-                    var selectedURLs = [URL]()
-                    for await url in taskGroup {
-                        if let url {
-                            selectedURLs.append(url)
+                    for (index, result) in results.enumerated() {
+                        taskGroup.addTask {
+                            let url = await self.processResult(result)
+                            return (index, url)
                         }
                     }
                     
-                    return selectedURLs
+                    var selectedURLs = [URL?](repeating: nil, count: results.count)
+                    for await (index, url) in taskGroup {
+                        if let url {
+                            selectedURLs[index] = url
+                        }
+                    }
+                    
+                    return selectedURLs.compactMap { $0 }
                 }
                 
                 photoLibraryPicker.callback(.selectedMediaAtURLs(selectedURLs))
diff --git a/ElementX/Sources/Services/Media/MediaUploadingPreprocessor.swift b/ElementX/Sources/Services/Media/MediaUploadingPreprocessor.swift
index a408fb77d..459e561d6 100644
--- a/ElementX/Sources/Services/Media/MediaUploadingPreprocessor.swift
+++ b/ElementX/Sources/Services/Media/MediaUploadingPreprocessor.swift
@@ -101,23 +101,26 @@ struct MediaUploadingPreprocessor {
     /// and its associated details or any resulting error
     func processMedia(at urls: [URL], maxUploadSize: UInt) async -> Result<[MediaInfo], MediaUploadingPreprocessorError> {
         await withTaskGroup { taskGroup in
-            for url in urls {
+            for (index, url) in urls.enumerated() {
                 taskGroup.addTask {
-                    await processMedia(at: url, maxUploadSize: maxUploadSize)
+                    let result = await processMedia(at: url, maxUploadSize: maxUploadSize)
+                    return (index, result)
                 }
             }
             
-            var mediaInfos = [MediaInfo]()
-            for await result in taskGroup {
+            // Store results in their respective index as they come in
+            var results = [MediaInfo?](repeating: nil, count: urls.count)
+            
+            for await (index, result) in taskGroup {
                 switch result {
                 case .success(let mediaInfo):
-                    mediaInfos.append(mediaInfo)
+                    results[index] = mediaInfo
                 case .failure(let error):
                     return .failure(error)
                 }
             }
             
-            return .success(mediaInfos)
+            return .success(results.compactMap { $0 })
         }
     }